Sodium Hydroxide → 215316-49-7

HRID 322844Notes

Reaction equation

HRID 322844 reaction equation
C([O:3][C:4](=[O:19])[CH2:5][C:6]([OH:18])([CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:7][CH2:8][CH3:9])C.[OH-].[Na+]>CO>[OH:18][C:6]([CH2:10][CH2:11][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)([CH2:7][CH2:8][CH3:9])[CH2:5][C:4]([OH:19])=[O:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 10149285Ethyl 3-hydroxy-3-(2-phenylethyl)hexanoate

Product 1

HCID 10285942215316-49-7

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Ethyl-3-hydroxy-3-(2-phenylethyl)hexanoate (II, EXAMPLE 1, 200 mmol) is dissolved in methanol (423 ml) and 2M sodium hydroxide (150 ml, 300 mmol) is added. The reaction mixture is stirred at 20-25° overnight. Methanol is removed and the remaining aqueous mixture is acidified with hydrochloric acid (4 M). The desired product is extracted into methyl t-butyl ether and dried over magnesium sulfate. The product is concentrated to give the title compound, TLC Rf=0.10 (ethyl acetate/hexane, 30/70); NMR (CDCl3) 7.43-7.13, 2.77-2.62, 2.06, 1.87-1.76, 1.63-1.57, 1.45-1.31 and 0.93 L; CMR (CDCl3) 176.9, 141.9, 128.4, 128.3, 125.9, 73.4, 42.7, 41.4, 40.9, 31.9, 17.0 and 14.5 L; MS (CI, ammonia) m/z (relative intensity) 254 (100), 236 (28), 218 (3), 194 (3), 159 (5).

Workup

  1. customMethanol is removed
  2. extractionThe desired product is extracted into methyl t-butyl ether
  3. dry with materialdried over magnesium sulfate
  4. concentrationThe product is concentrated

Sources & evidence

ORD record
ord-e6a0463278e8473cb0b3fd420379cdab
Source dataset
uspto-grants-2001_04
Patent number
US06211386B1

Reaction notes

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